title: Thiopyrano[2,3-e]indol-2-ones: angelicin heteroanalogues with potent photoantiproliferative activity.
abstract: A new class of compounds, the thiopyrano[2,3-e]indol-2-ones, bioisosters of the angular furocoumarin angelicin, was synthesized with the aim of obtaining new photochemotherapeutic agents. In particular 7,8-dimethyl-thiopyranoindolone 6c s showed a remarkable phototoxicity and a great dose UVA dependence reaching IC(50) values at submicromolar level. This latter photoinduced a massive apoptosis and a remarkable photodamage to lipids and proteins. Although it did not intercalate DNA, it was able to cause photooxidation of DNA bases.
authors.affiliation: Dipartimento Farmacochimico, Tossicologico e Biologico Università degli Studi di Palermo, Via Archirafi 32, 90123 Palermo, Italy.
authors.forename: Paola
authors.initials: P
authors.lastname: Barraja
authors.forename: Patrizia
authors.initials: P
authors.lastname: Diana
authors.forename: Alessandra
authors.initials: A
authors.lastname: Montalbano
authors.forename: Anna
authors.initials: A
authors.lastname: Carbone
authors.forename: Girolamo
authors.initials: G
authors.lastname: Cirrincione
authors.forename: Giampietro
authors.initials: G
authors.lastname: Viola
authors.forename: Alessia
authors.initials: A
authors.lastname: Salvador
authors.forename: Daniela
authors.initials: D
authors.lastname: Vedaldi
authors.forename: Francesco
authors.initials: F
authors.lastname: Dall'acqua
mesh_terms: D017209:Apoptosis; D004247:DNA / Q000528:radiation effects; D004249:DNA Damage; D011564:Furocoumarins / Q000737:chemistry*; D018922:HL-60 Cells; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D019169:Jurkat Cells; D015227:Lipid Peroxidation / Q000528:radiation effects; D008928:Mitochondria / Q000187:drug effects / Q000378:metabolism; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011506:Proteins / Q000378:metabolism; D014407:Tumor Cells, Cultured; D014466:Ultraviolet Rays
chemical_list: D011564:Furocoumarins; D007211:Indoles; D017319:Photosensitizing Agents; D011506:Proteins; D004247:DNA; C011659:angelicin